This article attempts to list the oldest houses built in the Commonwealth of Massachusetts, United States, from 1660 to 1679. These are known as First Period houses of the early to mid–second generation as they were built by the children of the first settlers in the Massachusetts Bay colony. During this time, buildings in New England were increasingly designed and built by regionally trained carpenters and were only occasionally influenced by new immigrant craftsmen. These structures have highly decorated wooden frames and are structurally more complex than the previous surviving generation of houses. While many existing homes are thought to have been built between 1660 and 1679, scientifically proving their age is another matter. Of the 78 houses on this list, just 11 have been proven through dendrochronology. The rest of the examples are approximate (indicated with a "circa" or "c.") and based on architectural studies and historical records. Only First-period houses built before 1679 by the second generation are suitable for inclusion on this list.
All entries should include citations concerning 17th-century architectural features, a report by an architectural historian, or dendrochronology whenever possible. The houses on this list are limited to extant structures preferably with remaining 17th-century architecture. Any given house may or may not have been moved over time from its original foundation.
Legend
1660–1669